Chicago’s Office Market: Where to Play Now

Register Now

March 18, 2026


Chicago Board of Trade
141 W. Jackson Blvd., 2nd Floor Conference Center
Chicago, IL 60604

Moderator

Speakers

Join NAIOP Chicago on Wednesday, March 18th and hear from leaders in the Chicago Office sector.  Our speakers will discuss current leasing trends, tenant demands, and the opportunities emerging in today’s office landscape!

Moderator:
Zack Cupkovic | Partner | R2 Companies

Guest Speakers:
Matt Carolan | Vice Chairman | JLL

Ellen May | Managing Director, Leasing Chicago | Tishman Speyer

Bryan Rosenberg | Managing Director | Eastdil Secured

Location:
Chicago Board of Trade
141 W. Jackson Blvd
2nd Floor Conference Center
Chicago, IL 60604
*A Photo ID will be required

Schedule of Events:
8:00 AM | Registration
8:30 AM | Program
9:30 AM | Adjourn

Registration Fees:

  • NAIOP Members – $75
  • DL Members – $65
  • Nonmembers – $95

Register Online
Download.pdf

​Registration Deadline: Monday, March 16, 2026

Matt Carolan

JLL
Vice Chairman

Matt co-lead’s a team of real estate brokers that assist companies in managing their corporate real estate portfolios. He and his team help advise companies on managing their entire portfolio. Matt believes technology is the future of real estate, so he and his team incorporate that into their management of real estate portfolios. They also provide expertise in representing companies internationally in the acquisition and disposition of offices and data centers. His team has represented corporations on deals in excess of $15 billion.

Matt’s mission is to exceed client expectations in every way, and technology is a key differentiator for him. He believes technology is the future in real estate and leveraging it is how his clients will succeed. Clients often want technology to support their business; he goes beyond those expectations and offers technology to them that they didn’t know existed.

Matt was honored to be awarded the “Broker of the Year” four times in Chicago and has been named “Crain’s 40 under 40” for his market leading experience in representing office and data center users. As a member of the JLL National Data Center team, he can offer a unique insight to his clients around acquiring and disposing of data centers. He has completed over 5 million square feet of real estate transactions for corporate users and over 250 mw of data center transactions.

 

Ellen May

Tishman Speyer
Managing Director, Leasing Chicago

Ellen May joined Tishman Speyer in 2007 and currently spearheads leasing efforts in the Chicago area, where she has been responsible for driving repositioning and leasing efforts most notably at The Franklin and Tishman Speyer’s newest development 320 North Sangamon. Prior to joining Tishman Speyer, Ellen was leasing director at Equity Office Properties in Chicago, where she was responsible for over 4 million square feet of leasing activities, including at such signature properties as the CME Center. She has almost 20 years of experience in marketing and leasing commercial real estate, with a particular focus on the Chicago area. Ellen is a board member of the Chicago Office Leasing Brokers Association and holds a BA from the University of Iowa.

Bryan Rosenberg

Eastdil Secured
Managing Director

 

Bryan Rosenberg is a Director in the Chicago office of Eastdil Secured with more than 14 years of experience in real estate and finance. He is responsible for advising clients on Real Estate capital markets transactions across the United States with a focus on Office and Healthcare assets Nationwide. Throughout his career, Bryan has been involved in more than $13 billion in investment sale and recapitalization transactions.  Prior to joining Eastdil Secured in 2019, he was a Director in HFF’s Chicago office.

Bryan is a licensed Real Estate Salesperson in the State of Illinois and holds a B.S. in Finance from Miami University.  He is a member of the NAIOP Real Estate Investment & Development I National Forum.

Zack Cupkovic

R2 Companies
Partner

Since joining R2 in 2012, Zack has been directly involved in acquiring +$800 million of real estate assets in markets across the U.S., specifically Creative Office, Experiential Retail & Hospitality, Multifamily, Flex Industrial and Single-Tenant NNN. Zack participates in all fundraising activities at R2, including the development of R2’s Fund strategies (R2 Yield, R2 Flagship).

In 2015, Zack led R2’s Goose Island 2025 masterplan that received recognition in national publications. He has lectured on the subject at multiple Universities. Zack is also a Board Member of Urban Rivers, a non-profit tasked by the City of Chicago with the creation of The Wild Mile, a mile-long eco-park on the east side of Goose Island.

Zack earned his Bachelor’s degree in English Literature & Architecture from Washington University in St. Louis.